Dichloromethane → Butyl α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-furanacetate

HRID 2420013Notes

Reaction equation

HRID 2420013 reaction equation
[CH2:1]([O:5][C:6](=[O:20])[CH:7](OC(=O)C)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4].[O:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.C(Cl)Cl>B(F)(F)F.CCOCC.C(OCC)(=O)C>[CH2:1]([O:5][C:6](=[O:20])[CH:7]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C:22]1[O:21][CH:25]=[CH:24][CH:23]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6344Dichloromethane3×HCID 8029FuranHCID 20312395HCID 20312395, compound

Product 1

HCID 54559425Butyl α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-furanacetate

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.6 g. (0.006 mol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester and 0.7 g. (0.01 mol.) of redistilled furan in 75 ml. of methylene chloride was cooled to -78° and four drops of boron trifluoride etherate was added with stirring. The reaction mixture was warmed to room temperature and left for 3 hours. Chromotography on silica gel with methylene chloride and methylene chloride containing increasing amounts of ethyl acetate gave the title compound.

Sources & evidence

ORD record
ord-573683eb7cb1427fbb9b8272e3d65d03
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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